| Identification | More | [Name]
DIBENZYLIDENEACETONE | [CAS]
538-58-9 | [Synonyms]
1,5-DIPHENYL-1,4-PENTADIEN-3-ONE
1,5-DIPHENYL-3-PENTADIENONE
1,5-DIPHENYL-PENTA-1,4-DIEN-3-ONE
AKOS 213-33
DBA
DIBENZAL ACETONE
DIBENZYLIDENEACETONE
DISTYRYL KETONE
TRANS,TRANS-1,5-DIPHENYL-1,4-PENTADIEN-3-ONE
TRANS,TRANS-1,5-DIPHENYLPENTA-1,4-DIEN-3-ONE
TRANS,TRANS-DIBENZALACETONE
TRANS,TRANS-DIBENZYLIDENEACETONE
TRANS,TRANS-DISTYRYL KETONE
(1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one
1,4-Pentadien-3-one, 1,5-diphenyl-
1,5-Diphenyl-1,4-pentadiene-3-one
1,5-diphenyl-4-pentadien-3-one
Bis(2-phenylvinyl) ketone
Styrol ketone
1,5-Diphenyl-3-Pentadieneone | [EINECS(EC#)]
208-697-5 | [Molecular Formula]
C17H14O | [MDL Number]
MFCD00004790 | [Molecular Weight]
234.29 | [MOL File]
538-58-9.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow powder | [Melting point ]
107-113 °C
| [Boiling point ]
336.62°C (rough estimate) | [density ]
1.0477 (rough estimate) | [refractive index ]
1.5000 (estimate) | [storage temp. ]
0-6°C | [form ]
solid | [color ]
yellow | [Stability:]
Stable. Incompatible with strong oxidizing agents. Combustible. | [InChI]
InChI=1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H | [InChIKey]
WMKGGPCROCCUDY-UHFFFAOYSA-N | [SMILES]
C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1 | [CAS DataBase Reference]
538-58-9(CAS DataBase Reference) | [EPA Substance Registry System]
1,4-Pentadien-3-one, 1,5-diphenyl- (538-58-9) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [TSCA ]
TSCA listed | [HS Code ]
2914790090 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow powder | [Uses]
Dibenzylideneacetone is used as a ligand to prepare palladium catalysts, which are widely used in catalytic hydrogenation, coupling, carbonylation, alkyne ring trimerization, etc. | [Preparation]
Dibenzylideneacetone is obtained by the reaction of benzaldehyde and acetone. The reaction was carried out in aqueous ethanol solution at a reaction temperature of 20-25°C with a yield of 78%. | [Synthesis Reference(s)]
Chemistry Letters, 9, p. 51, 1980
The Journal of Organic Chemistry, 45, p. 3840, 1980 DOI: 10.1021/jo01307a022
Organic Syntheses, Coll. Vol. 2, p. 167, 1943 | [Biological Activity]
Dibenzylideneacetone (DBA) showed inhibitory activity against Botrytis cinerea Chitinase with an IC50 of 13.10 μg/mL. The MIC of DBA against B. cinerea was 32 μg/mL, and the EC50 values for inhibition of hyphae growth and spore germination were 16.29 and 14.64 μg/mL, respectively. DBA was able to significantly extend the shelf life of cherry tomato shelf life and is a promising antifungal agent for fruit preservation[1]. | [Purification Methods]
Crystallise the ketone from hot ethyl acetate (2.5mL/g) or EtOH. [Beilstein 7 IV 1747.] | [References]
[1] XIAODI NIU; Chenyang W; Ziyou Wang, HONGSU WANG*. Dibenzylideneacetone Overcomes Botrytis cinerea Infection in Cherry Tomatoes by Inhibiting Chitinase Activity[J]. Journal of Agricultural and Food Chemistry, 2023. DOI:10.1021/acs.jafc.3c05695. |
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